Title: Islesboro Vacation Packages & Trips 2026 | Expedia.ca [Hotels in Islesboro](https://expedia.ca/Islesboro-Hotels.d6339925.Travel-Guide-Hotels)[Vacation Rentals in Islesboro](https://expedia.ca/Islesboro-Vacation-Rentals.d6339925.Travel-Guide-VacationRentals)[Flights to Islesboro](https://expedia.ca/Cheap-Flights-To-Islesboro.d6339925.Travel-Guide-Flights)[Islesboro Car Rentals](https://expedia.ca/Car-Rentals-In-Islesboro.d6339925.Car-Rental-Guide) ![](https://images.trvl-media.com/place/6339925/09d4e36c-169f-4ff4-a573-9f2becf5ef64.jpg?impolicy=fcrop&w=1200&h=300&q=medium) # Islesboro Vacation Packages ## Book a Hotel + Flight or Car together to unlock savings Photo by Colleen Johnson - ## Plan, book, travel with confidence - ### Better together Save up to CA $1,096 when you book a flight and hotel together\* - ### Find the right fit With over 300,000 hotels worldwide, it's easy to create a perfect package - ### Rest easy Plan, book, and manage your trip all in one place #### Your Islesboro Vacation When you organize a vacation package to Islesboro, you can relax and enjoy your getaway knowing your travel plans are in order. Discover the many charms of this amazing city from your base in a neighborhood like Bayside, which is great for history. If sightseeing is on the agenda during your trip to Islesboro, stop by major attractions like [Windsor Chairmakers](https://www.expedia.ca/Windsor-Chairmakers-Lincolnville.d553248633992553803.Vacation-Attraction), [Schoolhouse Museum](https://www.expedia.ca/Schoolhouse-Museum-Lincolnville.d553248621532668344.Vacation-Attraction) and [Warren Island State Park](https://www.expedia.ca/Warren-Island-State-Park-Maine.d637213991769526272.Vacation-Attraction). A few quick clicks is all it takes to build your ideal Islesboro vacation on Expedia. ## Ready to book your vacation to Islesboro? Choose your dates ## Islesboro Hotel Deals ![Island log home in Maine with ocean views](https://images.trvl-media.com/lodging/36000000/35170000/35164700/35164619/a90dad88_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Island log home in Maine with ocean views Islesboro ME 10/10 Exceptional! (88 reviews) Everything was perfect! The downside was that the stay was cut short as our work finished early1 Reviewed on Dec 12, 2025 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=35164619&PinnedHotelID=35164619&HadPinnedHotel=true®ionId=6339925) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=35164619&PinnedHotelID=35164619&HadPinnedHotel=true®ionId=6339925) ![Trade Winds on the Bay](https://images.trvl-media.com/lodging/96000000/95450000/95445100/95445009/6e8014d1_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### Trade Winds on the Bay 2 Park Dr Rockland ME Fully refundableReserve now, pay when you stay 8.4/10 Very Good! (338 reviews) Clean, large room. Friendly staff. Great location@ Reviewed on Jan 26, 2026 [Get rates](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=95445009&PinnedHotelID=95445009&HadPinnedHotel=true®ionId=6339925) [](https://expedia.ca/Hotel-Search?startDate=21%2F02%2F2026&endDate=22%2F02%2F2026&selected=95445009&PinnedHotelID=95445009&HadPinnedHotel=true®ionId=6339925) ![The Country Inn at Camden Rockport](https://images.trvl-media.com/lodging/2000000/1570000/1570000/1569993/63281d3f_y.jpg?impolicy=resizecrop&rw=340&ch=150) ### The Country Inn at Camden Rockport 8 Country Inn Way Rockport ME Fully refundableReserve now, pay when you stay CA $176 CA $192 total Feb 11 - Feb 12 includes taxes & fees 9.4/10 Exceptional! (1,000 reviews) The Inn is very charming and well maintained. the staff were courteous and attentive. the breakfasts were good and the cleaning staff was wonderful. The pool and hot tub were the main feature and look forward to visiting in the summer. Reviewed on Jan 24, 2026 [](https://expedia.ca/Hotel-Search?startDate=11%2F02%2F2026&endDate=12%2F02%2F2026&selected=1569993&PinnedHotelID=1569993&HadPinnedHotel=true®ionId=6339925) [See all 1,303 properties in Islesboro](https://expedia.ca/Hotel-Search?rfrrid=TG.LP.Hotels.Package&startDate=08%2F02%2F2026&endDate=09%2F02%2F2026®ionId=6339925) Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply. ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/all-inclusive_holidays_US.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) All Inclusive Vacations [](https://expedia.ca/lp/theme-vacations/all-inclusive-vacations?rfrr=editorial.All_Inclusive%20Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/XPC_Beach_Overview_HR_v3.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Beach Vacations [](https://expedia.ca/lp/theme-vacations/beach-vacations?rfrr=editorial.Beach_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/06/08/Family_holidays_US_3_.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Family Vacations [](https://expedia.ca/lp/theme-vacations/kid-friendly-vacations?rfrr=editorial.Family_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/04/29/frCA_Sejours_golf-Portugal.jpeg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Golf Vacations [](https://expedia.ca/lp/theme-vacations/golf-vacations?rfrr=editorial.Golf_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/07/15/US_Luxury_VR_Miami.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Luxury Vacations [](https://expedia.ca/lp/theme-vacations/luxury-vacations?rfrr=editorial.Luxury_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/08/29/romantic.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Romantic Vacations [](https://expedia.ca/lp/theme-vacations/romantic-vacations?rfrr=editorial.Romantic_Vacations.click) ![](https://forever.travel-assets.com/flex/flexmanager/images/2022/10/17/31952_v1_atfraraski22_insta_4.jpg?impolicy=fcrop&w=300&h=300&q=mediumHigh) Ski Vacations [](https://expedia.ca/lp/theme-vacations/ski-vacations?rfrr=editorial.Ski_Vacations.click) ## Explore a world of travel with Expedia \* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. ![](https://a.travel-assets.com/mad-service/footer/bnaBanners/BEX_Footer.jpg) ## Go further with the Expedia app Save on select hotels and earn double points when you book on the app. Our app deals help you to save on trips so you can travel more and manage it all on the go. Scan the QR code with your device camera and download our app